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Liquid Silicone Copolymers

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Liquid Silicone Copolymers Office europeen des brevets (fi) Publication number : 0 555 050 A1 @ EUROPEAN PATENT APPLICATION @ Application number : 93300752.8 @ Int. CI.5 : C08G 77/06, C08L 83/04 (22) Date of filing : 02.02.93 (So) Priority : 06.02.92 US 832065 @ Inventor : Traver, Frank John 1 Downey Road Troy, New York 12180 (US) (43) Date of publication of application : Inventor : Ward, Brian John 11.08.93 Bulletin 93/32 R.D. 1, Box 236 Valley Falls, New York 12185 (US) Inventor : Delker, Wayne Lee @) Designated Contracting States : 1 Imperial Court DE ES FR GB IT NL Ballston Lake, New York 12019 (US) Inventor : Thimineur, Raymond Joseph 162 Willow Lane @ Applicant : GENERAL ELECTRIC COMPANY Scotia, New York 12302 (US) 1 River Road Schenectady, NY 12345 (US) (74) Representative : Pratt, Richard Wilson et al London Patent Operation G.E. Technical Services Co. Inc. Essex House 12/13 Essex Street London WC2R 3AA (GB) (54) Liquid silicone copolymers. (57) A process for the production of liquid copolymers having R3SiO05 units and Si02 units comprises reacting a hydrolyzable triorganosilane with an alkyl orthosilicate in the presence of water and an aliphatic hydrocarbon solvent having from 6 to 15 carbon atoms and an aromatic hydrocarbon content of less than 0.5 percent by weight based on the total weight of the solvent. < O IO o 10 10 10 o Q_ LU Jouve, 18, rue Saint-Denis, 75001 PARIS EP 0 555 050 A1 The present invention relates to the production of a novel family of liquid copolymers having R3SiO0.5 units and Si02 units. More particularly the present invention relates to copolymers, commonly known as MQ resins, which are produced in novel liquid form by a hydrolys is reaction in an aliphatic hydrocarbon solvent having from 6 to 15 carbon atoms. Such polymers have substantial utility in compositions in which solid counterparts 5 prepared in aromatic solvents would not be suitable, especially in personal care products. BACKGROUND OF THE INVENTION Silicone materials are well-known and are highly regarded for their high temperature capabilities, for their 10 resistance to the elements and for their good low temperature properties. In addition, silicon compositions are good electrical insulating materials. Resinous copolymers composed of R3SiO0.5 units and Si02 units are well known in the art and are descri- bed in, for example, Dexter, United States Patent No. 2,736,721; Currie, United States Patent No. 2,814,601; Goodwin, United States Patent No. 2,857,356; and Modic, United States Patent No. 3,205,283. These copo- 15 lymers are prepared by hydrolyzing a hydrolyzable triorganosilane, such as trimethylchlorosilane, with an alkyl orthosilicate, such as ethyl orthosilicate, or the partial hydrolyzate of such alkyl orthosilicate. The hydrolysis is generally conducted in the presence of a small amount of water and in the presence of a suitable aromatic organic solvent, such as toluene or xylene. These resin copolymers are in the form of a solid resin product and have been found to be useful in many 20 commercial applications. They have been reported to be useful in the preparation of high strength organopo- lysiloxane compositions. See, Jeram et al., United States Patent No. 3,884,866. Their use in preparing room temperature vulcanizable (RTV) silicone rubbers has also been noted, such as in Smith, United States Patent No. 4,490,500. Saad, United States Patent No. 4,247,441 teaches preparing silicone molding compositions having excellent electrical properties. The use of the silicone resin copolymers inadhesive compositions is also 25 well known in the art and is described in Horning, United States Patent No. 4,016,328; and Blizzard, United States Patent No. 4,255,316. More recently, such copolymer resins are finding use in personal care products, i.e., in compositions for use on the skin, e.g., as antiperspirants, sunscreens, lotions, and the like. However, the use of toluene and other aromatic hydrocarbons as the solvent in the synthesis of the silicone 30 copolymers has increasingly become a concern because trace amounts of aromatic hydrocarbons such as tol- uene in the product resin requires special labelling, especially for personal care products, and in some instanc- es there is a very low tolerance level for aromatic residues. It has therefore become necessary to find a re- placement for toluene as a solvent in the hydrolyzation process to produce silicone copolymers. Further, the prior art silicone copolymers are produced in a powdery form which requires the addition of 35 solvents in order to affix the powdery silicone copolymers with silicone fluids. These solvents must then be removed. It would therefore represent an advance in the art if a silicone copolymer could be prepared having increased solubility in silicone fluids. Still further, the prior art silicone copolymers do not dissolve readily in higher viscosity fluids. This detri- mental characteristic further limits the use of these copolymers in personal care compositions such as skin 40 lotions and sunscreeens. It has now been surprisingly found that by employing an aliphatic hydrocarbon of from 6 to 15 carbon atoms as the solvent for the hydrolyzation reaction, a novel silicone copolymer is produced in the liquid form which is substantially free from any aromatic hydrocarbons and which has improved solubility in silicone resin fluids and other solvents. Unexpectedly, as shown in the working examples of the instant specification, these novel 45 silicone copolymers can be dissovled in high proportions in high molecularweightfluids. this excellent property provides a formulating flexibility to the end user, enabling the preparation of protective skin care products. SUMMARY OF THE INVENTION 50 According to the present invention there is provided a novel liquid silicone copolymer substantially free from any aromatic hydrocarbon impurities comprising R3SiO0.5 units and Si02 units wherein R is a monovalent hydrocarbon radical selected from the group consisting of alkyl radicals of from 1 to 8 carbon atoms, alkenyl radicals of from 1 to 8 carbon atoms, cycloalkyl radicals, mononuclear aryl radicals and haloalkyl radicals, pre- pared by a process comprising hydrolyzing a hydrolyzable triorganosilane with an alkyl orthosilicate in the pres- 55 ence of water and an aliphatic hydrocarbon of from 6 to 1 5 carbon atoms having an aromatic hydrocarbon con- tent of less than 0.5 percent by weight based on the total weight of the solvent. Preferably the aliphatic hydrocarbon solvent comprises n-hexane, the alkyl orthosilicate comprises ethyl orthosilicate, the hydrolyzable triorganosilane comprises trimethylchlorosilane, and the liquid copolymer com- 2 EP 0 555 050 A1 prises from about 0.5 to about 1.0 R3SiO0.5 units per Si02 units. Also according to the present invention there is disclosed an improved process for preparing a silicone copolymer comprising R3SiO0.5 units and Si02 units wherein R is a monovalent hydrocarbon radical selected from the group consisting of alkyl radicals of 1 to 8 carbon atoms, alkenyl radicals of 1 to 8 carbon atoms, cy- 5 cloalkyl radicals, mononuclear aryl radicals and haloalkyl radicals comprising hydrolyzing a hydrolyzable trior- ganosilane with an alkyl orthosilicate in the presence of water, the improvement comprising carrying out the hydrolyzation reaction in the presence of an aliphatic hydrocarbon solvent of from 6 to about 15 carbon atoms having an aromatic hydrocarbon content of less than 0.5 percent by weight based on the weight of the solvent, wherein said copolymer is in the liquid form and is substantially free of any aromatic hydrocarbon impurities. 10 Substantially free is defined for purposes of the present invention as having less than trace amounts of the impurity. DETAILED DESCRIPTION OF THE PRESENT INVENTION 15 The present invention provides novel liquid silicone copolymers, also known as MQ resins, having R3SiO0.5 units and RSi02 units. These copolymers are prepared by hydrolyzing a hydrolyzable triorganosilane with an alkyl orthosilicate orthe partial hydrolyzate of such alkyl orthosilicate in the presence of water and an aliphatic hydrocarbon solvent having from 6 to about 15 carbon atoms having an aromatic hydrocarbon content of less than 0.5 percent by weight based on the total weight of the solvent. During the cohydrolysis of the triorgano- 20 silane and alkyl orthosilicate, most of the silicon bonded halogen and the silicon bonded alkoxy groups are replaced by silicon-bonded hydroxyl groups through which the two organosilicon materials condense to form siloxane linkages. The liquid copolymer is generally soluble in the organic aliphatic hydrocarbon solvent and insoluble in the water present in the hydrolysis reaction system, and the organic aliphatic hydrocarbon layer therefore contains the resinous copolymer. This organic solvent layer containing the liquid copolymer is sepa- 25 rated from the aqueous layer and in some cases washed several times with water to provide the liquid copo- lymer in the organic aliphatic hydrocarbon solvent relatively free of either hydrochloric acid which results from the hydrolysis of the alkanol which results from the hydrolysis. The aliphatic hydrocarbon solvent used in the hydrolysis reaction which forms the resinous copolymer can vary within wide limits. Typically they comprises aliphatic hydrocarbons having from 6 to about 15 carbon 30 atoms. Preferred are hexane, heptane, octane, nonane, decane, undecane, dodecane, tridecane, tetradecane, pentadecane, hexadecane, isomers thereof and mixtures of any of the foregoing. Most preferred is n-hexane. These materials are well known to those skilled in the art and are available commercially. Also preferred for use in the present invention are the isoparaffinic aliphatic solvents. A particulary pre- ferred commercial isoparaffinic aliphatic solvent is lsopar®E, Exxon Corporation, which is an isoparaffinic sol- 35 vent of principally C8 isomers. Other preferred commercial solvents are lsopar®C, G, H, K, L and M which are all isoparaffinic aliphatic solvents, the latter comprising a mixture of mainly C13-C16 isomers.
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